| Identification | Back Directory | [Name]
secoxyloganin | [CAS]
58822-47-2 | [Synonyms]
secoxyloganin
Secoxyloganin, >=98%
Secologanoside 11-methyl ester
(2S)-3α-Ethenyl-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid
(2S,3R,4S)-2-(β-D-Glucopyranosyloxy)-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]aceticaci
2H-Pyran-4-acetic acid,3-ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-,(2S,3R,4S)-
2H-Pyran-4-acetic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2S,3R,4S)- | [Molecular Formula]
C17H24O11 | [MDL Number]
MFCD20260822 | [MOL File]
58822-47-2.mol | [Molecular Weight]
404.37 |
| Chemical Properties | Back Directory | [Boiling point ]
649.5±55.0 °C(Predicted) | [density ]
1.49±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
DMF: 5mg/mL; DMSO: 5mg/mL; Ethanol: 10mg/mL; PBS (pH 7.2): 10mg/mL | [form ]
A crystalline solid | [pka]
4.40±0.10(Predicted) | [color ]
White to light yellow | [Major Application]
food and beverages | [InChIKey]
MQLSOVRLZHTATK-PEYNGXJCSA-N | [SMILES]
O1[C@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)O[C@@H]2OC=C([C@H]([C@H]2C=C)CC(=O)O)C(=O)OC |
| Hazard Information | Back Directory | [Description]
Secoxyloganin is a secoiridoid glycoside that has been found in L. japonica and has diverse biological activities.1,2,3 It is active against E. coli and S. aureus in a disc assay when used at a concentration of 2 mg/disc.1 Secoxyloganin is cytotoxic to human dermal fibroblasts (IC50 = 78.1 μM).2 In vivo, secoxyloganin (10 mg/ml) prevents hen egg white lysozyme-induced decreases in tail vein blood flow, a marker of allergic inflammation, in hen egg white lysozyme-sensitized mice.3 | [Chemical Properties]
Light brown amorphous powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the Caprifoliaceae plant honeysuckle or honeysuckle. | [Uses]
Secoxyloganin is a component of Poraqueiba sericea stems and may be used for its cytotoxic activity. | [Definition]
ChEBI: Secoxyloganin is a secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding beta-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties. It has a role as a plant metabolite, an antioxidant and an anti-allergic agent. It is a methyl ester, a member of pyrans, an enoate ester, a beta-D-glucoside, a monosaccharide derivative, a dicarboxylic acid monoester and a secoiridoid glycoside. It is a conjugate acid of a secoxyloganin(1-). | [References]
[1] JIANHUA XIONG. Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leaves[J]. Food Chemistry, 2013, 138 1: Pages 327-333. DOI: 10.1016/j.foodchem.2012.10.127
[2] ILHEM ZEBIRI . Biological activities of triterpenoids from Poraqueiba sericea stems[J]. Natural Product Research, 2017, 31 11: Pages 1333-1338. DOI: 10.1080/14786419.2016.1241998
[3] HISAE OKU. Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonica.[J]. Biological & pharmaceutical bulletin, 2011, 34 8: 1330-1333. DOI: 10.1248/bpb.34.1330 |
|
|